In my mid-20s, following a series of fortunate events, I found myself in the position of being treated to a very fine bespoke suit. It was, I knew, a rare opportunity to own the kind of clothing I’d be unlikely able to afford for another decade. Seeking maximum suit mileage, I opted for a versatile charcoal grey, and this being not-my-money, a fantastically expensive Zegna fabric. The suit would be stain-proof and crease-proof, and in the hands of a master tailor, foolproof. Right?

Wrong. I was young, not yet sure enough of my taste to dispute a “master” anything. He steered me away from the super-slim look I requested, toward a more traditional cut. The result was everything you’d expect from 50-odd hours of highly skilled labour: it was exquisite. And I hated it.

It was, of course, my fault. I should have been clearer and firmer. I also shouldn’t have left that shop unhappy. And I should not have conflated technical skill and knowledge with aesthetic judgment.

According to John Der Shahinian, who runs the Montreal tailoring shop, Arthur, with his father and brother, being a good tailor isn’t the same as having good taste. “Bespoke is about making a suit from scratch the way the client likes it—even if it means doing things we don’t agree with,” he says. “It’s so important for clients to tell us what they like. A lot of people just say, ‘I trust you, make me look good.’ But that gets tricky.”

In this view, the tailor is a craftsman—technically proficient and unbound by personal preferences. With specific direction, he’ll produce precisely what is demanded, whether that’s a slim-fitting handmade suit or tweaking an off-the-rack jacket to look nearly as good. But what if you don’t have an opinion about sleeve pitch? What if you think dart placement refers to sports and gorge lines are a geological phenomenon? Inevitably, you’ll get whatever the tailor thinks is best. Which is great, if you and your tailor happen to share the same taste.

“It’s so important to find a tailor that suits your sensibility,” says Sydney Mamane, a tailor who owns the Toronto menswear boutique, Sydney’s. “Every tailor has their own opinion on how things should look and feel. And most tailors are very, very, very slow to change. They’re afraid to break tradition. And that’s where people run into problems.” For Mamane, the tailor isn’t merely an artisan, but an artist. “I’m not interested in producing to produce,” he says. “I’m quite rigid with my aesthetic.” Mamane flatly refuses to do wide lapels, long jackets or highly structured shoulders. (Little surprise, perhaps, that he’s recently shifted focus from bespoke to his menswear line, Kin, offering made-to-measure alterations on a single style.) If only all tailors could be so principled—and stubbornly honest. Mamane’s case is extreme, but it underlines a crucial point: any tailor with 10,000 hours of experience can do a bang-up job hemming trousers, but when it comes to style, there’s no guarantee that you’ll like that tailor’s work. Sometimes bad suits happen to good tailors.

So if you want to avoid a $5,000 let-down, arm yourself with convictions about lapels, cuffs and vents in advance. And bring pictures.